Cash Forshee moved to Nashville as a young man, determined to make his mark in the music industry. But he decided he wanted to tackle something more meaningful in life, so he started studying sociology and business and moved into the health-care world. At 25, happy leading an internal sales consulting unit at a publicly traded company, he received an offer to work for a health-care startup. After endless discussions with friends and colleagues, he made the jump, and is now senior vice-president at Medalogix, which uses data to improve patient health.

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The decision to switch came to him at 1:47 a.m. It was instinct. He knew he had to take the offer. But being of an analytical bent, he decided to set out some powerful questions that others – particularly from the millennial generation – might ask themselves when confronted with such a choice. In an entry on the Brazen Careerist blog and in an interview, Mr. Forshee shared eight of them:

1. Does it motivate you to learn something new?

We’ve been told that specializing is important, an idea that hits home as young people pick university majors, seek their first job, and start to climb the corporate totem pole. But he believes that specializing early can limit your potential and stunt your self-discovery. “The value I bring to my team members and the company is based on my experiences rather than any one skill,” he said in the interview. “So at an early stage you have to consider how to gain experience at a broad level.”

Yes, there’s a place for mastery of a topic. But not, he believes, at the expense of having a broader understanding. So when evaluating a career option, consider whether it can stretch you and build new experiences. You might also want to follow his technique of every three months picking a topic you want to learn more about, and then contacting others and reading to learn more. He is currently probing pricing psychology, and will share what he has found with his team.

2. Does it push you to learn something about yourself?

Mr. Forshee suggests that you place greater weight on the exploration and development possibilities if a new position, rather than the immediate responsibilities or job title. Generally, we create a mental image of ourselves and what we want our career to be. But that can be limiting. “A career is a journey of self-discovery,” he insists. So remain open to – indeed, seek – opportunities outside the self-image you have, learning what other talents will emerge.

3. Does it scare you?

Be afraid. Not very afraid, but a bit afraid. We grow when we extend beyond our limits and take on challenges. He urges you to understand your fears, but recognize that staying in the comfortable sweet spot you have carved out will prevent growth, which is what careers are about. Medalogix was a startup and he knew that 90 per cent of startups fail. So it was scary. But he’s happy with his choice.

4. Does it scare your friends and family?

You’ll probably seek counsel from your friends and family about your possible new role. They want to protect you, and so they may be nervous. Understand where that timidity comes from, and why it could signal, counterintuitively, that the career choice is a challenge to embrace. “It’s a loving bias. They want you to succeed and be in a place where your psychology and emotions are not put at risk. But you need to take risks and challenge yourself,” Mr. Forshee said.

5. Does it change the way you evaluate success?

Often we evaluate success by our bank balance. But in the spirit of challenging yourself, he urges you to take career paths that expand your notions of success. “What I was looking for at 23 is different from [what I want] now, at 27, and it will change in the years ahead,” he noted.

6. Will it surround you with passionate people?

You need to be around people who inspire and challenge you. Not just a good boss, for example, but a passionate boss. The greatest leaders, he argues, are passionate and can translate that spirit so it energizes the people they work with. “This is big: We spend a third of our lives at work, surrounded by colleagues,” he said.

7. Does it excite you to talk about it?

Notice if you are constantly rambling on to friends about this opportunity – that’s obviously a good sign. “Tally the number of times the opportunity organically comes to mind. Pay attention to what you’re thinking. Is it the experience? Earnings potential? Outcomes? There’s no wrong answer, but understanding your own drivers and interests will give you insight into what’s most important about your potential next step,” he writes.

8. Will the job change you?

This question wasn’t on his original list, but Mr. Forshee said during the interview that you should ask it anyway. We all want to shape our careers. But there’s also a value in letting our jobs shape us in unexpected ways – in being open to the transformation that a new environment might provide. “It’s an artful balance,” he concludes.

Harvey Schachter is a Battersea, Ont.-based writer specializing in management issues. He writes Monday Morning Manager and management book reviews for the print edition of Report on Business and an online work-life column Balance. E-mailHarvey Schachter

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